I keep a writing journal that I enjoy writing in. I also have a lot of old journal with writing that I'd love to digitize but am too lazy to retype. What is a good, accurate, OCR program that would let me scan my writings and would then convert it to a word document?

If you're using a PC, one program you may already have that's quite good at OCR is Microsoft OneNote. Just import a scanned image, right-click and select Edit Alt Text. You can then copy the OCRed text to any program you want. It's not as good as a professional, dedicated OCR program, but it's quite good for quick and cheap conversion.

It is maybe not considered OCR. But you could consider using crowd sourcing for this task. There are two websites that facilitate this. There are Amazon's Mechanical Turk or vWorker.com. In the first you pay pennies to let anonymous workers do small fractions of your text. At vworker you could just upload all the work and let the workers decide what they want to get paid.

I'm a translator and often receive documents from clients that are either un-tagged, image-only PDFs or paper documents. One thing I like about Adobe's OCR is that it will recognize many source languages (which may not be useful to the OP, but may be useful to someone reading this answer later).

If you are talking about hand-writing and not something created by a typewriter or a computer print out the best you'll be able to do is scan it as a graphic object with a scanner.

If you are talking about output from a printer or typewriter it will depend on the font to some degree. Some OCR better that others. If you have printed output ABBY Finereader does a good job but will require clean-up/editing.

If you are looking for something free and decent try MeOCR Image to Text Converter It works better than the other free ones I've tried like FreeOCR and SimpleOCR and it gives you formatted output that can be edited easily. The other ones just give you the text but its not formatted it makes me waste a lot of time reformatting also its pretty simple to use. Anyway that's my 2 cents worth hope it helps.